GB963829A - 17ª‡,21-alkoxy-methylenedioxy pregnenes and pregnadienes and process therefor - Google Patents

17ª‡,21-alkoxy-methylenedioxy pregnenes and pregnadienes and process therefor

Info

Publication number
GB963829A
GB963829A GB22744/62A GB2274462A GB963829A GB 963829 A GB963829 A GB 963829A GB 22744/62 A GB22744/62 A GB 22744/62A GB 2274462 A GB2274462 A GB 2274462A GB 963829 A GB963829 A GB 963829A
Authority
GB
United Kingdom
Prior art keywords
steroids
dihydroxy
acyloxy
acid
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB22744/62A
Inventor
Alberto Ercoli
Rinaldo Gardi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Francesco Vismara SpA
Original Assignee
Francesco Vismara SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DEV21321A external-priority patent/DE1173897B/en
Application filed by Francesco Vismara SpA filed Critical Francesco Vismara SpA
Publication of GB963829A publication Critical patent/GB963829A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises steroids of the general formulae: <FORM:0963829/C1/1> <FORM:0963829/C1/2> wherein X represents a methylene, b -hydroxymethylene, or carbonyl group, Y represents hydrogen or fluorine, R represents an alkyl group containing 1 to 3 carbon atoms and R1 represents hydrogen, chlorine or fluorine or a methyl group, and the preparation thereof by reacting the corresponding 17a , 21 - dihydroxy - 20 - keto - steroids with an excess of the required alkyl orthoformate in the presence of an acid catalyst, for example an aromatic sulphonic acid, a Lewis acid such as stannic chloride or antimony pertochloride, or a salt of an organic base with a mineral acid such as pyridine hydrochloride. 2-Methyl-D 4-3, 20-diketo-17a , 21-dihydroxysteroids are prepared by reacting steroids of the first general formula above with diethyl oxalate and sodium methoxide, treating the resulting corresponding 2-enolate with methyl iodide to form the corresponding 2-methyl compound, and removing the grouping protecting the 17-dihydroxy-acetone side chain with a mineral acid in hot methanol. 11b -Acyloxy-17a , 21-dihydroxy-steroids are prepared by treating steroids of the above general formulae wherein X represents hydroxymethylene in the first general formulae with an acylating agent to form the corresponding 11b -acyloxy compounds, and then hydrolysing the 17a , 21-alkoxymethylene group with a mineral acid. 11b , 21-Dihydroxy-D 16-steroids are prepared by dehydrating at the 16, 17-position the above 11b -acyloxy-17a , 21-dihydroxy-steroids with phosphorus oxychloride or thionyl chloride and then hydrolysing the 11b -acyloxy group in the resulting 11b -acyloxy-21-hydroxy-D 16-steroids. 17a -Monoformates of 17a , 21-dihydroxy-steroids are prepared by hydrolysing the 17a , 21-alkoxy-methylenedioxy steroids of the above general formulae with dilute mineral acid or with an organic acid to form a mixture of the 17a -monoformates and 21-monoformates and separating the two formates from one another. Specification 894,168 is referred to.
GB22744/62A 1961-06-24 1962-06-13 17ª‡,21-alkoxy-methylenedioxy pregnenes and pregnadienes and process therefor Expired GB963829A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT1165961 1961-06-24
DEV21321A DE1173897B (en) 1961-06-24 1961-09-18 Process for the preparation of cyclic 17ª ‡, 21-orthoformic acid esters of? -3-keto steroids

Publications (1)

Publication Number Publication Date
GB963829A true GB963829A (en) 1964-07-15

Family

ID=26001548

Family Applications (2)

Application Number Title Priority Date Filing Date
GB22744/62A Expired GB963829A (en) 1961-06-24 1962-06-13 17ª‡,21-alkoxy-methylenedioxy pregnenes and pregnadienes and process therefor
GB22743/62A Expired GB996080A (en) 1961-06-24 1962-06-13 17-monoesters of 17ª‡,21-dihydroxy steroids and process for the preparation thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB22743/62A Expired GB996080A (en) 1961-06-24 1962-06-13 17-monoesters of 17ª‡,21-dihydroxy steroids and process for the preparation thereof

Country Status (4)

Country Link
US (1) US3152154A (en)
CH (1) CH429716A (en)
DE (1) DE1195748B (en)
GB (2) GB963829A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024045950A1 (en) * 2022-08-29 2024-03-07 扬州奥锐特药业有限公司 Steroid compound and crystal form a thereof, and preparation methods therefor and use thereof

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1047518A (en) * 1963-06-11 1966-11-02 Glaxo Lab Ltd 17ª‡-monoesters of 11,17,21-trihydroxy steroid compounds
GB1070751A (en) * 1964-01-28 1967-06-01 Glaxo Lab Ltd 17-esters of 17-hydroxy-21-desoxy-steroids
US3499081A (en) * 1966-12-21 1970-03-03 Squibb & Sons Inc 9-chloroprogestational agents
US3502700A (en) * 1967-01-19 1970-03-24 Squibb & Sons Inc 17-esters of 9alpha,21-dihalo-11beta,17alpha-dihydroxyprogesterones
FR2029415A1 (en) * 1969-01-30 1970-10-23 Ciba Geigy Ag 2-chloro-6alpha 9alpha-difluoro-16alpha-methylpregna-1
IT1033042B (en) * 1970-03-14 1979-07-10 Luso Farmaco Inst DESAMETAZONE 17 VALERATO AND PROCESSES FOR ITS PREPARATION
US3694471A (en) * 1970-06-08 1972-09-26 Warner Lambert Pharmaceutical 17-valerate ester of 6{60 ,9{60 -difluorohydrocortisone, its compositions and use as an anti-inflammatory agent
US3857941A (en) * 1970-06-22 1974-12-31 Warner Lambert Co Pharmaceutical compositions and use of prednisolone 17-benzoate
US3789121A (en) * 1971-11-26 1974-01-29 Warner Lambert Co 17{60 ,21-orthobutyrates of 6{60 , 9{60 -difluoro-hydrocortisone and 6{60 , 9{60 -difluoroprednisolone, compositions containing same and the use thereof as anti-inflammatory agents
US4036831A (en) * 1975-10-28 1977-07-19 Steroid Development Company Establishment Trimethyl siloxane steroid intermediates
NZ185295A (en) * 1976-10-04 1980-04-28 Schering Ag 9-chloroprednisolone derivatives and pharmaceutical compositions
DE2735110A1 (en) * 1977-08-04 1979-02-15 Hoechst Ag CORTICOID-17-ALKYLCARBONATE AND METHOD FOR THE PRODUCTION THEREOF
JPS6040439B2 (en) * 1978-03-29 1985-09-11 大正製薬株式会社 hydrocortisone derivatives
EP0029924B1 (en) * 1979-11-16 1984-08-15 STEROSYNT Ltd. 6-alpha-fluoro-16-methyl-prednisolone-17,21 diesters and pharmaceutical compositions containing them
US4318853A (en) * 1980-01-31 1982-03-09 The Upjohn Company 9β,11β-Epoxy-5β-corticoids
US4353985A (en) * 1980-07-14 1982-10-12 Schering Aktiengesellschaft Process for the preparation of 11 β-hydroxy steroids
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE
DE3401680A1 (en) * 1984-01-16 1985-07-18 Schering AG, 1000 Berlin und 4709 Bergkamen 6 (ALPHA), 16SS DIMETHYL CORTICOIDS
ITMI20011762A1 (en) 2001-08-10 2003-02-10 Cosmo Spa 17ALPHA ESTERS, 21-DIHYDROXYPREGNENE, THEIR USE AS ANTI-ANDROGENETIC AGENTS AND PROCEDURES FOR THEIR PREPARATION
ITMI20071616A1 (en) 2007-08-03 2009-02-04 Cosmo Spa ENZYMATIC PROCESS FOR THE OBTAINING OF 17-ALFA MONOESTERS OF CORTEXOLONE AND / OR ITS 9,11-DEIDRODERIVATI.
EP3006453A1 (en) 2014-10-08 2016-04-13 Cosmo Technologies Ltd. 17alpha-monoesters and 17alpha,21-diesters of cortexolone for use in the treatment of tumors
EP3108879A1 (en) 2015-06-25 2016-12-28 Cassiopea S.p.A. High concentration formulation
FR3115284B1 (en) 2020-10-19 2023-12-08 Ind Chimica Srl PROCESS FOR PREPARING 21-(ACETYLOXY)-17-(1-OXOPROPOXY)-PREGN-4-ENE-3,20-DIONE
IT202100008429A1 (en) 2021-04-06 2022-10-06 Farmabios Spa Process for the preparation of cortexolone 17α-propionate and its new hydrated crystalline form
CN116135871A (en) * 2021-11-16 2023-05-19 石家庄迪斯凯威医药科技有限公司 Antibacterial compound with drug resistance

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2932656A (en) * 1957-06-19 1960-04-12 Merck & Co Inc Production of delta1, 4-3, 20-diketopregnadienes from the corresponding semicarbazones
US2971886A (en) * 1957-11-27 1961-02-14 Upjohn Co 1-dehydro-17-hydroxyprogesterone acylates and therapeutic composition thereof
US2864839A (en) * 1958-07-25 1958-12-16 Olin Mathieson delta4, 7, 9(11)-pregnatriene-17alpha, 21-diol-3, 20-dione and process therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024045950A1 (en) * 2022-08-29 2024-03-07 扬州奥锐特药业有限公司 Steroid compound and crystal form a thereof, and preparation methods therefor and use thereof

Also Published As

Publication number Publication date
US3152154A (en) 1964-10-06
CH429716A (en) 1967-02-15
GB996080A (en) 1965-06-23
DE1195748B (en) 1965-07-01

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